


Dating

by Mare_Nubium



Category: Harry Potter - J. K. Rowling, How to Train Your Dragon (Movies), Rise of the Guardians (2012)
Genre: Alternate Universe - Hogwarts, M/M
Language: English
Status: In-Progress
Published: 2014-06-26
Updated: 2014-06-30
Packaged: 2018-02-06 08:09:44
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 3,202
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1850749
Author URL: https://archiveofourown.org/users/Mare_Nubium/pseuds/Mare_Nubium
Summary: <blockquote class="userstuff">
              <p>Fourth year Gryffindor Jackson Overland has finally had enough of the sort of but not quiet flittering going on between him and the scary fifth year Hufflepuff Toothless so he dose something about it. At the same time his brother, Fourth year Slytherin Jack Overland is being overly flirty and touchy with Toothless' cousin and fellow Hufflepuff Hiccup, but neither one will admit to liking one another even though everyone can see they do.</p>
            </blockquote>





	1. Fed up

**Author's Note:**

  * For [Dragonlover496](https://archiveofourown.org/users/Dragonlover496/gifts).



It was a relatively calm day at Hogwarts, students were milling around as usual. Slytherins were picking on other students though they stayed clear of the two hufflepuffs that sat under the shade of a tree. Now they weren’t afraid of the younger boy with the small frame and gap teeth but they were afraid of his cousin. Most of the populace were afraid of the ebony haired boy with the piercing green eyes and the dragon tooth necklace. The only ones not afraid of the boy, known as Toothless, were about a handful of various students, most of them being friend with Hiccup. No one really just approached the boy it was usually Hiccup they wanted to speak to, not to say Toothless was a bad person. In fact he was very kind and protective, but he did intimidade people badly. That’s why it came as a shock for everyone in the area, except for Hiccup who muttered ‘about time’ when the brunet Overland twin walked over. 

The Overland twins were an odd duo, they were almost identical except for hair and eye color. Were the older boy had Brown hair and brown eyes his brother had white hair and blue eyes. The brunet, Jackson Alexander Overland was a Gryffindor while Jack Frost Overland was a Slytherin, but you couldn’t find a closer pair of siblings. The pair had been adopted into Professor North’s little family when they were about ten and with their aunt Anna and Uncle Sandy also being professors and their older brother Aster going to school they spent much of their time there as well.

Jackson marched right up to the two boys, ignoring the looks he was getting as he did so. Once he neared Toothless sent the boy a questioning look. Besides Hiccup Jackson was the only other one he was actually comfortable around. It came as a great shock as Jackson yanked Toothless’ tie hard enough to pull the older boy up then smash their lips together. It was silent as Jackson thoroughly snogged the other before backing up. Toothless stared at the other in shock with wide eyes and a blush. huffing slightly, trying to regain his breath, Jackson also had a light blush on his face.

“Huh?” came Toothless’ intelligent question. Jackson just gave a little shrug, not meeting the other’s gaze.

“I got tired of waiting.” Hiccup elbowed his cousin hard when all the older boy did was stare. For all the courage Jackson had he had started to fidget nervously, wondering if he had misread the signs the other had given. Blinking out of his state of shock the Hufflepuff blurted out quickly and quiet loudly,

“Willyougooutwithme?” Jackson blinked in confusion, tilting his head to the side.

“What?” Toothless swallowed nervously, his eyes now locked onto the brown orbs in front of his.

“Will… will you go out with me?” Slowly a bright grin filled Jackson’s face.

“I would love to.” With a small smile of his own Toothless relaxed.

“Cool, uh, so er… how about this Saturday, during the Hogsmeade trip?”

“That sounds great, I’ll see you then.” Jackson pressed a quick kiss to Toothless’ cheek before running off. Hiccup laughed lightly as his cousin stared after the retreating boy with a small, goofy smile on his face.

“HA!” a Slytherin 7th year shouted, “The big bad Hufflepuff’s bent! ANd for that pathetic Gryffindor too!” Toothless whole demeanor changed at once. He stood growling at the other, scarring many students close by. Before he could get there though the boy was on the ground holding his nose in pain.

“I told you to leave my brother alone.” snarled a white haired boy, his blue eyes set in a menacing glare.

“You’ll regret this Overland.” That caused the boy to scoff.

“Yeah right, whatever.” The boy walked over where the two Hufflepuffs still where. He sighed as he looked to Toothless.

“I suppose I really should be doing the whole ‘you hurt my brother I’ll hurt you’ spiel but I actually like you and know you aren’t that sort of person so I’m going to just skip over that whole thing.” Both Hiccup and Toothless blinked at the teen in shock.

“What?”

“We thought you didn’t like him.” admitted Hiccup.

“No way, trust me if I didn’t like him I wouldn’t pull fun pranks on him. I would be aiming to hurt him. I mean why did you think Pitch ended up in the Hospital wing after my last one?” Jack asked as he spun his wand, which was more of a staff.

“Well that’s good to know. It would be awkward to date Jackson if you hated me.” Before Jack could respond the bell rang.

“Whelp, come on Hiccup. Off to Herbology.” Jack used the hooked end of his staff to catch the shorter boy around the waist.

“I’ll see you at dinner.” Hiccup called to Toothless who was headed for Care of Mythical Creatures. He then turned to Jack with an unamused look.

“And just what do you think you are doing Mr. Overland?”

“Well I happened to have seen a really cute guy so I just had to get his attention.” Jack sent him a wink, still dragging him by his staff, “Have I seen you somewhere before?”

“Yes and that’s why I don’t go there anymore.” Hiccup deadpanned. Jack winced a little, smirk still in place.

“Ouch Hic, right in the heart.”

“Maybe if you tried better pick up lines.” Jack perked up at once, once again sure of himself.

“Aw, you love my pick up lines, no matter how cheesy they are.”

“I draw the line at innuendos involving brooms, dragons and wands.” Hiccup informed before slipping out of the staff and making his way into the greenhouse. Jack watched him enter while leaning against his staff. An arm wrapped around the boy’s shoulders causing the teen to look up. He was met with brown eyes and a smug smirk.

“What?” Jack asked the taller boy.

“Still hitting on Haddock, huh? Why not just ask the guy out already?” Flynn Rider, or as less people know Eugene, questioned. Jack scowled a little, shrugging the fellow SLytherin’s arm off.

“I’m not hitting on him. We’re just messing around.” Flynn wiggled his eyebrows while responding with,

“If you go out with him then you really can be messing around.” Jack gave his friend a blank face. The boy rolled his eyes.

“Come on Jack, there’s more sexual tension between you two then there is between Anna and Kristoff.” Jack didn’t respond this time and just went in for class. Flynn sighed and threw his hands in the air.

“Boys!” He said in exasperation.


	2. Hogsmeade

It was time for the Hogsmeade trip and Jack watched in amusement as Jackson fretted with his outfit.

“Jack.” came the whine. Jack stood up and looked through his brother’s chest and pulled out a pair of jeans, a tee shirt and a button up shirt with sleeves to the elbow. He gave the clothes a once over then glanced to his brother before tapping the clothes. The tee shirt turned a pale blue while the button up shirt turned a tan. The jeans were now a dark blue in color. Jackson smiled as he got dressed. Jack sat picking at the sleeve of his ever present blue hoodie while he waited. When Jackson was done they headed out of the Gryffindor common room and went to the doors. There they saw Toothless and Hiccup already waiting. The older boy was wearing a dark purple dress shirt with black pants. He was currently glaring at a group who were looking over at him and giggling. Hiccup wore a dark green long sleeved shirt with a brown sweater vest over it and brown pants.

“H-Hi.” Jackson stuttered out with a blush. Toothless stopped his glaring to look at Jackson. He blinked twice before a light blush appeared on his face.Glancing away he paused before speaking,

“Hey… you look really nice.” Jackson shrugged shyley with an excited smile in place.

“Thanks, Jack had to pick the clothes out though, I’m rubbish when it comes to it.”

“Only when you're nervous.” Jack corrected, “Now come on before the carriages leave.” The group of four made their way down to the front gates at a leisurely pace.

“So where’s ‘Punzie and Merida?” Hiccup asked.

“Merida got herself a DT thanks to Snape and Rapunzel is off doing something with Flynn.” Jack informed. Hiccup hummed in response. Jack sort of zoned out after that, thinking about what the taller Slytherin had been saying to him. The boy had been pressuring him more and more to ask Hiccup out. A glance to Hiccup then back to the ground and Jack was frowning in thought. Yeah Hiccup was a pretty cool guy and really feisty for a Hufflepuff. Where Toothless tended to scare people Hiccup wasn’t intimidating but he sure had a mouth. The kid would get in trouble with other students for his sassy remarks towards bullies. It was pretty cute and then whenever he smiled with that adorable awkwardness and showing the little gap between his teeth. Yeah Jack could admit Hiccup was really good looking but that didn’t mean he was flirting with him… right? Jack shook his head clear of the thoughts, blinking and looking to his brother.

“You say something?” Jackson was looking at him in slight worry.

“You zoned out dude, we’re at the carriages.”

“Hm, we are.” Jack noted. Climbing in he decided to sit next to Hiccup, forcing Jackson and Toothless to sit next to each other. Both boys blushed, a scowl aimed at the white haired teen. Jack merely smirked back, knowing his brother enough to know that it was more of embarrassment than actual anger. Toothless on the other hand he decided to ignore since he had no idea what the boy was thinking. Jackson’s giggling caught everyone’s attention though.

“What?” Jack asked in suspicion. Jackson waved his hand, trying to calm down.

“I was just remembering something.”

“And that would be?” Toothless asked. Jackson bit his lip before answering,

“It was one of the times I tagged along with Jack when he was asking a girl out. It was for a dance going on. I honestly can’t believe he got the girl the pick up line he used was god awful.”

“What was it?” Hiccup asked this time.

“Do you live in a corn field, cause I’m stalking you.” The Hufflepuffs stared at him. Jack shrugged, completely at ease with the whole thing.

“I was really hoping she’d say no so I wouldn’t have to go. Of course I ask the one girl who actually thought it was so sweet.” Jackson snickered with a wide smile.

“She ended up stalking Jack for a year.” Toothless snorted, a smirk on his face.

“Any other embarrassing dating stories?” Hiccup asked.

“Oh you have no idea.” Jackson smirked smugly.

“Like you’re one to talk! You were steady with a girl and broke up with her in class.”

“That’s awful!” cried Hiccup, eyes wide. Jack snickered while Jackson hid his face, face bright red.

“Not how he did it. Okay so we ended up in a lot of the same classes based on last names, well what happened was it was really loud and Jackson was talking, right? Well he started shouting when the teacher silenced the class and he ended up shouting: I’m breaking up with you because I’m gay in a silent classroom. The girl was cool about it, he got teased but never bullied. The school was chill.”

“God that was awful!”

“But look at it this way, Rapunzel became one of our closest friends.”

“Wait, you dated Rapunzel?”

“For, like, a month.” Jackson admitted.

“It was funny because you know how the person breaking up is usually all ‘but I still want to be friend’? Rapunzel said and I quote : I will not let you break up with me unless you promise that we will still be friends.”

“Hiccup convinced himself that he was straight and had a crush on Astrid for several years, even though she beat him up a lot.” Toothless informed, a smirk aimed at his cousin.

“God don’t remind me,” moaned Hiccup. Jack looked towards the boy with a raised brow.

“You’re gay?” he was met with two flat stares from both green eyed boys.

“You have been hitting on him not even knowing?” Toothless asked.

“He does that a lot. A lot of times he’ll flirt just to bug people so it never mattered the preference. Hell he’s hit on girls who have had girlfriends. Pissed them off to no end until they found out his preference.”

“How can you tell when he’s serious?” Hiccup asked, eyeing jack distrustfully.

“Biggest thing? He won’t use the god awful lines, he’ll use the sweeter ones like Because of you, I laugh a little harder, cry a little less, and smile a lot more or Hey, don't frown. You never know who could be falling in love with your smile.” Jack pointedly ignored the look Hiccup was giving him. Of all the lines Jackson had to say it had to be that one. He could still remember that day and judging by the look Hiccup did too.

 

***FLASHBACK***  
 _Jack was running down the hallway trying to get to the hospital wing. Jackson had fallen off his broom and even though Aster was there he had to see his brother. As he skidded around a corner he noticed a boy curled up against a wall. Jack stopped, recognizing the boy as Hiccup, a Hufflepuff._

_“Are you okay?” Jack asked as he knelt beside the boy. Hiccup looked up with tear filled eyes._

_“Hey what’s wrong?” The confusion in the other’s eyes was both adorable and heart breaking._

_“W...Why do you care?” He had asked quietly. Jack could understand where the boy was coming from, Slytherins weren’t known for being caring after all._

_“I don’t like seeing people sad,” he admitted then sent a smirk and a wink, “Especially really cute guys.” Hiccup had let out a bitter chuckle at that._

_“Right, who would think this,” he gestured to all of him, “was cute?”_

_“Someone who thinks green is the prettiest color for eyes and that freckles are adorable. Someone who can see just how caring and smart you are.” Hiccup couldn’t stop the shy, embarrassed smile but that soon disappeared back into a frown._

_“Hey, don’t frown. You never know who could be falling in love with your smile.” Hiccup had laughed at that._

_“That was awful… thanks for trying though um…”_

_“Jack, Jack Frost Overland.” Jack greeted with a beaming smile._

_“Hiccup Horrendous Haddock the third.” Jack helped the boy up._

_“So where are you going Mr. Haddock?”_

_“Uh, the hospital wing. My cousin got injured catching a kid who fell off their broom.” Jack snickered._

_“I am never going to let him live that down.” he decided. At Hiccup’s questioning look he replied._

_“The kid who fell off his broom was my brother Jackson.”_

***END FLASHBACK***

 

Jack slammed his head against the window.

“Jack?” called Jackson in worry. Jack waved his older brother off. He had just made a realization that he wasn’t sure how to feel about. Eugene was right. He had been flirting with Hiccup. He really did like the boy. Now what was he supposed to do?

“Okay, really what’s going on?” Jackson demanded. Jack just gave his brother a look that said ‘not now’. Jackson responded with his own look telling his brother that they would be talking. And that moment came too soon when they made it to the village.

“Sorry, just a minute okay?” Jackson asked as he started to pull his brother away.

“No, it’s fine, we do have all day.” Toothless answered. Jackson smiled until they were out of earshot.

“What’s going on?”

“Rider has been pressuring me into asking Hiccup out because he said we were flirting and I just came to the conclusion a few minutes ago that yes I was flirting with him.” Jackson gave him a blank look.

“You just now realized that? Wow.”

“Jacks what do I do?”

“Ask him out,” the brunette replied as though it were obvious. Jack paced while running a hand through his hair.

“How? Do I just ask him? How do I know if he’s even interested? Is he even interested? Should I ask Toothless first?” Jackson had opened his mouth before shutting it then asking,

“Ask Toothless?”

“Yeah, I mean should I ask him if it’s okay to date Hiccup before asking Hiccup? Or should I just, I don’t know. I think I should ask him first...”

“...You think you should ask Toothless’ permission to date his cousin?” Jackson clarified. Jack nodded with a bright red face. Jackson thought something over then nodded.

“Okay, wait here.” Jack did as his older brother requested. Jackson made his way over to the cousins.

“Hey Toothless? Jack wanted your opinion on something.” The green eyed boy sent his date a confused look but didn’t question it. 

Jack played with his hands as he paced back and forth.

“Jack?” came Toothless’ questioning voice, “Jackson said you wanted my opinion on something?” Jack swallowed nervously.

“Not exactly.” He mumbled. Closing his eyes he took a deep breath before locking gazes with the taller boy.

“I… I would like your permission to d-date Hiccup.” Jack ignored the fact that his voice cracked as well as the heat prickling at his face. His gaze never wavered though. Toothless looked shocked.

“You’re… asking me if it’s okay to date Hiccup?” Jack nodded, throat dry.

“Why? I mean why wouldn’t you just ask Hiccup out if you wanted to date him?” Jack bit his lip while struggling to find the words he wanted.

“ I respect you. I have seen and heard what you have done for Hiccup, and even though you’re cousins you two are more like brothers, and there have even been times where you have been like a dad to him. He means a lot to you and you mean a lot to him. It wouldn’t feel right to ask him out without you saying it’s okay.”

“I guess I pegged you wrong.” Jack gave a slight smirk in response.

“No, you have me pegged right, I just like surprising people.” It was silent for a few more minutes as Toothless thought. Jack played with his fingers as he waited.

“Alright. You trust me enough to date your brother so I’m going to trust you enough to date Hiccup. I do have to say it’s about time. I was starting to think neither of you were going to make a move.”

“Huh?” Toothless smiled, it was small and almost unseen but it was there.

“He’s liked you for a while.” Jack’s jaw fell open as he stared at the older boy in shock.

“R-really?” Toothless nodded while his smile grew from the barley seen one. He gave a nod back in the direction from where they came.

“Come on, our dates are waiting.” Jack could only grin as he followed the older student

**Notes for the Chapter:**

> I'M SORRY! Toothless seems sooooo out of character and ugh! I LOVE him but hate trying to write him.

**Author's Note:**

> Okay so I have no idea where I came up with the idea of Human!Toothless and Jackson but I thought it would be adorable so I wrote it. When it comes to the whole Hufflepuff thing, yes I know Hiccup is crazy smart but I decided Hufflepuff for him in this fic because 1) who wouldn't love sassy Hufflepuff Hiccup? and 2) He is insanely loyal to Toothless and anyone who denies so need to watch the movies more. I thought it would be funny for Toothless to be in Hufflepuff mostly because he would be a scary one. 
> 
> This is a gift to my friend because she encourages me to write (and finish) my messed up fics, helps me with story plots and doesn't diss the parings I like even if she doesn't. Love ya Babs, you annoying Gryffindor ;P
> 
> Any tips on improvement would be amazing.
> 
> No I could not come up with a more creative title and that one pick up line I found on tumblr with Jack and Hiccup and had to use it. If I find it again I'll put the person's user name.


End file.
